Evidence map›Paper›PMID 29693690›Full record

ArticleOrganic & biomolecular chemistry2018

Glycosyl nitrates in synthesis: streamlined access to glucopyranose building blocks differentiated at C-2.

Tinghua Wang, Swati S Nigudkar, Jagodige P Yasomanee, Nigam P Rath, Keith J Stine, Alexei V Demchenko

Abstract read
In one paragraph

Article in Organic & biomolecular chemistry, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.

0numbers the graph read from it
0cells of the map it votes in
6citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

6 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Esters of Glucose-2-Phosphate: Occurrence and Chemistry.Molecules (Basel, Switzerland) · 2020
    Article
  5. Review
  6. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

6 authors.

Tinghua WangDepartment of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Swati S Nigudkar
Jagodige P Yasomanee
Nigam P Rath
Keith J Stine
Alexei V Demchenko

Funding

Automation of the chemical synthesis of human milk oligosaccharidesR01GM111835 · NIGMS · SAINT LOUIS UNIVERSITY · PI DEMCHENKO, ALEXEI V · 2014 to 2023
$2.5M
Refinement and implementation of the automated oligosaccharide synthesizerU01GM120673 · NIGMS · UNIVERSITY OF MISSOURI-ST. LOUIS · PI DE MEO, CRISTINA, DEMCHENKO, ALEXEI V · 2016 to 2019
$2.2M
NIGMS NIH HHS R01 GM111835NIGMS NIH HHS U01 GM120673
6 · The paper itself

Abstract

In an attempt to refine a CAN-mediated synthesis of 1,3,4,6-tetra-O-acetyl-α-d-glucopyranose (2-OH glucose) we unexpectedly discovered that this reaction proceeds via the intermediacy of glycosyl nitrates. Improved mechanistic understanding of this reaction led to the development of a more versatile synthesis of 2-OH glucose from a variety of precursors. Also demonstrated is the conversion of 2-OH glucose into a variety of building blocks differentially protected at C-2, a position that is generally hard to protect regioselectively in the glucopyranose series.

Indexed as

Chemistry Techniques, SyntheticGlucoseGlycosylationNitratesPyransGlucoseNitratesPyrans

Identifiers

PMID29693690
PMCPMC5971085

What OpenQuestion holds

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Registered trials

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.